N-[(1,3-Benzodioxol-5-yl)meth­yl]-4-methyl­benzamide: an analogue of capsaicin

Maganhi, S.H.; Damião, M.C.F.C.B.; Tavares, M.T.; Parise Filho, R.

doi:10.1107/S1600536813002201

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o332

doi:10.1107/S1600536813002201

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N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide: an analogue of capsaicin

Stella H. Maganhi,^a ^* Mariana C. F. C. B. Damião,^b Maurício T. Tavares ^b and Roberto Parise Filho ^b

^aDepartmento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil, and ^bDepartmento de Farmacia, Universidade de São Paulo, 05508-000 São Paulo, SP, Brazil
^*Correspondence e-mail: stellamaganhi@gmail.com

(Received 21 January 2013; accepted 22 January 2013; online 2 February 2013)

In the title compound, C₁₆H₁₅NO₃, the five-membered 1,3-dioxole ring is in an envelope conformation with the methylene C atom as the flap atom [lying 0.202 (3) Å out of the plane formed by the other four atoms]. The benzene ring makes a dihedral angle of 84.65 (4)° with the best least-squares plane through the 1,3-benzodioxole fused-ring system, which substitutes the 2-methoxyphenol moiety in capsaicin. In the crystal, molecules are connected into a zigzag supramolecular chain along the c-axis direction by N—H⋯O hydrogen bonds. These chains are connected into a layer in the ac plane by C—H⋯π interactions.

Related literature

For the biological activity of capsaicin, see: Okamoto et al. (2011 ). For ring conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₅NO₃
M_r = 269.29
Monoclinic, P 2₁ /c
a = 4.9810 (2) Å
b = 26.652 (1) Å
c = 10.0545 (3) Å
β = 92.139 (2)°
V = 1333.84 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 290 K
0.33 × 0.24 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: numerical (SADABS; Sheldrick, 1996 ) T_min = 0.940, T_max = 0.951
4550 measured reflections
2602 independent reflections
1698 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.03
2602 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3ⁱ	0.91	2.08	2.958 (2)	162
C7—H7A⋯Cg1	0.97	2.74	3.603 (3)	149
C16—H16C⋯Cg2	0.96	2.96	3.829 (2)	151
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1999 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: Marvinsketch (Chemaxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813002201/tk5191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002201/tk5191Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002201/tk5191Isup3.cml

checkCIF report

Comment top

Capsaicin is the main pungent compound found in chilli peppers of the genus Capsicum and is found to exert multiple pharmacological and physiological effects, including analgesic, anti-cancer, anti-inflammatory, anti-oxidant and anti-obesity (Okamoto et al. 2011). This makes capsaicin an excellent scaffold for the rational design of analogues with better biological activity. The title compound (I) is a capsaicin-like derivative where the 2-methoxyphenol ring was substituted with a benzodioxol ring and the amide aliphatic chain was replaced with a 4-methylbenzoyl group. As suitable crystals were obtained from its hexane solution, a crystal structure determination of (I) was undertaken.

In (I), Fig. 1, the 1,3-dioxole five membered ring is in an envelope configuration with the C7 atom lying 0.202 (3) Å out of the plane formed by the other four atoms. The ring puckering parameters are q₂ = 0.128 (2) Å and ϕ₂ = 149.9 (9)° (Cremer & Pople, 1975).

The crystal packing of (I), Table 1, is sustained by N—H···O and C—H···π interactions, leading to supramolecular layers in the ac plane.

Related literature top

For the biological activity of capsaicin, see: Okamoto et al. (2011). For ring conformational analysis, see: Cremer & Pople (1975).

Experimental top

1-(1,3-Benzodioxol-5-yl)methanamine (0.755 g, 5 mmol) was dissolved in chloroform (20 ml) and then triethylamine (411 µL, 5.5 mmol) and DMF (40 µL, 0,5 mmol) were added. The mixture was stirred for 30 min under argon atmosphere. 4-Methylbenzoyl chloride (661 µL, 5 mmol) was added in portions and stirred over 24 h. The organic layer was washed with 5% HCl aqueous solution, water, brine and dried over anhydrous Na₂SO₄. The solvent was removed under high vacuum and the title compound was obtained after recrystallization from hot hexane. Analytical data: white solid, yield 71.4° (0.96 g, 3.57 mmol). ¹H-NMR NMR (300 MHz, DMSO-d6, ppm): δ 8.87 (1H, bt, J = 5.8 Hz, 9-NH), 7.79 (2H, d, J = 8.2 Hz,12, 13-ArH), 7.27 (2H, d, J = 8.2 Hz, 14, 15-ArH), 6.83 (3H, m, 4, 5, 7-ArH), 5.98 (2H, s, 1-OCH₂O), 4.38 (2H, d, J = 6.0 Hz, 8-CH₂), 2.36 (3H, s, 15-CH₃). ¹³C NMR (75 MHz, DMSO-d6, ppm) δ: 165.9 (C9), 147.18 (C2), 145.98 (C1), 141.02 (C13), 133.68 (C10), 131.67 (C5), 128.77 (C12, C14), 127.21 (C11, C15), 120.42 (C4), 107.94 (C3), 107.92 (C6), 100.74 (C7), 42.36 (C8), 20.89 (C16); Anal. calcd. for: C₁₆H₁₅NO₃ (269.11): C 71.36, H 5.61, N 5.20, found: C 71.30, H 5.74, N 5.17, mp: 404.7–405.2 K.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012)\bbr00; software used to prepare material for publication: Marvinsketch (Chemaxon, 2010) and publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).

N-[(1,3-Benzodioxol-5-yl)methyl]-4-methylbenzamide top

Crystal data top

C₁₆H₁₅NO₃	F(000) = 568
M_r = 269.29	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5124 reflections
a = 4.9810 (2) Å	θ = 3.1–27.5°
b = 26.652 (1) Å	µ = 0.09 mm⁻¹
c = 10.0545 (3) Å	T = 290 K
β = 92.139 (2)°	Prism, colourless
V = 1333.84 (8) Å³	0.33 × 0.24 × 0.16 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2602 independent reflections
Radiation source: fine-focus sealed tube	1698 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 0 pixels mm^-1	θ_max = 26.0°, θ_min = 3.1°
ϕ and ω scans	h = −6→6
Absorption correction: numerical (SADABS; Sheldrick, 1996)	k = −32→30
T_min = 0.940, T_max = 0.951	l = −12→12
4550 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0859P)² + 0.0674P] where P = (F_o² + 2F_c²)/3
2602 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₆H₁₅NO₃	V = 1333.84 (8) Å³
M_r = 269.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9810 (2) Å	µ = 0.09 mm⁻¹
b = 26.652 (1) Å	T = 290 K
c = 10.0545 (3) Å	0.33 × 0.24 × 0.16 mm
β = 92.139 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2602 independent reflections
Absorption correction: numerical (SADABS; Sheldrick, 1996)	1698 reflections with I > 2σ(I)
T_min = 0.940, T_max = 0.951	R_int = 0.023
4550 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
2602 reflections	Δρ_min = −0.20 e Å⁻³
182 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	−0.0219 (3)	0.06137 (6)	0.88685 (15)	0.0754 (5)
O2	−0.0295 (3)	0.00662 (6)	0.71012 (17)	0.0797 (5)
O3	0.4080 (3)	0.24272 (5)	0.87268 (12)	0.0634 (4)
N1	0.4208 (3)	0.22490 (6)	0.65426 (14)	0.0496 (4)
H1N1	0.3768	0.2357	0.5702	0.060*
C1	0.1365 (4)	0.08000 (7)	0.78849 (19)	0.0525 (5)
C2	0.1354 (4)	0.04694 (8)	0.6838 (2)	0.0585 (5)
C3	0.2867 (5)	0.05485 (8)	0.5769 (2)	0.0733 (6)
H3	0.2878	0.0322	0.5065	0.088*
C4	0.4407 (4)	0.09851 (8)	0.5771 (2)	0.0649 (6)
H4	0.5483	0.1047	0.5053	0.078*
C5	0.4398 (3)	0.13305 (7)	0.68029 (18)	0.0503 (5)
C6	0.2825 (3)	0.12319 (7)	0.79020 (18)	0.0505 (5)
H6	0.2782	0.1453	0.8616	0.061*
C7	−0.1575 (5)	0.01955 (9)	0.8290 (2)	0.0740 (7)
H7A	−0.3444	0.0279	0.8094	0.089*
H7B	−0.1510	−0.0086	0.8903	0.089*
C8	0.5961 (4)	0.18139 (7)	0.6730 (2)	0.0556 (5)
H8A	0.7042	0.1856	0.7545	0.067*
H8B	0.7169	0.1795	0.5997	0.067*
C9	0.3359 (3)	0.25214 (7)	0.75640 (17)	0.0467 (5)
C10	0.1449 (3)	0.29384 (7)	0.72454 (16)	0.0440 (4)
C11	−0.0105 (4)	0.29652 (7)	0.60682 (19)	0.0547 (5)
H11	0.0065	0.2719	0.5422	0.066*
C12	−0.1888 (4)	0.33522 (8)	0.5853 (2)	0.0620 (6)
H12	−0.2918	0.3360	0.5062	0.074*
C13	−0.2198 (4)	0.37300 (7)	0.6775 (2)	0.0535 (5)
C14	−0.0639 (4)	0.37058 (8)	0.7936 (2)	0.0598 (5)
H14	−0.0779	0.3958	0.8570	0.072*
C15	0.1126 (4)	0.33142 (8)	0.81753 (18)	0.0576 (5)
H15	0.2117	0.3303	0.8977	0.069*
C16	−0.4161 (4)	0.41514 (8)	0.6534 (2)	0.0710 (6)
H16A	−0.3634	0.4345	0.5782	0.106*
H16B	−0.4180	0.4363	0.7307	0.106*
H16C	−0.5924	0.4016	0.6358	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0884 (10)	0.0677 (10)	0.0708 (10)	−0.0258 (8)	0.0130 (8)	−0.0058 (8)
O2	0.0972 (11)	0.0531 (9)	0.0875 (12)	−0.0117 (8)	−0.0135 (9)	−0.0127 (8)
O3	0.0857 (10)	0.0681 (10)	0.0363 (8)	0.0119 (8)	−0.0003 (6)	0.0050 (7)
N1	0.0628 (9)	0.0497 (9)	0.0366 (8)	0.0042 (7)	0.0049 (7)	0.0051 (7)
C1	0.0582 (11)	0.0506 (12)	0.0482 (11)	0.0027 (9)	−0.0053 (9)	−0.0010 (9)
C2	0.0697 (13)	0.0469 (11)	0.0577 (13)	0.0060 (10)	−0.0126 (10)	−0.0048 (10)
C3	0.1024 (17)	0.0590 (14)	0.0577 (14)	0.0133 (13)	−0.0077 (12)	−0.0177 (11)
C4	0.0821 (14)	0.0646 (14)	0.0486 (12)	0.0180 (11)	0.0101 (10)	−0.0022 (10)
C5	0.0545 (11)	0.0504 (11)	0.0459 (11)	0.0121 (9)	0.0000 (8)	0.0027 (9)
C6	0.0592 (11)	0.0481 (11)	0.0440 (11)	0.0028 (9)	0.0003 (8)	−0.0066 (9)
C7	0.0766 (14)	0.0614 (14)	0.0827 (17)	−0.0153 (12)	−0.0136 (13)	−0.0005 (12)
C8	0.0553 (11)	0.0590 (12)	0.0530 (11)	0.0067 (10)	0.0089 (8)	0.0053 (9)
C9	0.0559 (10)	0.0482 (11)	0.0361 (10)	−0.0035 (8)	0.0040 (8)	0.0042 (8)
C10	0.0507 (10)	0.0452 (10)	0.0365 (9)	−0.0044 (8)	0.0069 (7)	0.0020 (8)
C11	0.0632 (11)	0.0533 (12)	0.0474 (11)	0.0016 (9)	−0.0009 (9)	−0.0075 (9)
C12	0.0610 (12)	0.0660 (14)	0.0582 (13)	0.0061 (11)	−0.0090 (9)	−0.0025 (11)
C13	0.0481 (10)	0.0524 (12)	0.0605 (12)	−0.0026 (9)	0.0088 (9)	0.0040 (10)
C14	0.0707 (13)	0.0547 (13)	0.0544 (12)	0.0039 (10)	0.0093 (10)	−0.0095 (10)
C15	0.0712 (13)	0.0598 (13)	0.0417 (11)	0.0020 (10)	−0.0008 (9)	−0.0037 (9)
C16	0.0593 (13)	0.0664 (14)	0.0879 (17)	0.0101 (11)	0.0121 (11)	0.0065 (12)

Geometric parameters (Å, º) top

O1—C1	1.380 (2)	C7—H7B	0.9700
O1—C7	1.417 (3)	C8—H8A	0.9700
O2—C2	1.384 (2)	C8—H8B	0.9700
O2—C7	1.418 (3)	C9—C10	1.490 (3)
O3—C9	1.2358 (19)	C10—C15	1.384 (3)
N1—C9	1.339 (2)	C10—C11	1.392 (3)
N1—C8	1.459 (2)	C11—C12	1.373 (3)
N1—H1N1	0.9124	C11—H11	0.9300
C1—C6	1.361 (3)	C12—C13	1.382 (3)
C1—C2	1.372 (3)	C12—H12	0.9300
C2—C3	1.352 (3)	C13—C14	1.380 (3)
C3—C4	1.394 (3)	C13—C16	1.503 (3)
C3—H3	0.9300	C14—C15	1.380 (3)
C4—C5	1.387 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.403 (3)	C16—H16A	0.9600
C5—C8	1.508 (3)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—H7A	0.9700

C1—O1—C7	105.39 (16)	C5—C8—H8A	109.2
C2—O2—C7	105.13 (16)	N1—C8—H8B	109.2
C9—N1—C8	122.43 (15)	C5—C8—H8B	109.2
C9—N1—H1N1	117.9	H8A—C8—H8B	107.9
C8—N1—H1N1	119.5	O3—C9—N1	121.77 (17)
C6—C1—C2	122.7 (2)	O3—C9—C10	121.03 (16)
C6—C1—O1	127.92 (18)	N1—C9—C10	117.19 (15)
C2—C1—O1	109.40 (18)	C15—C10—C11	117.55 (17)
C3—C2—C1	121.5 (2)	C15—C10—C9	118.96 (16)
C3—C2—O2	128.7 (2)	C11—C10—C9	123.47 (17)
C1—C2—O2	109.73 (19)	C12—C11—C10	120.57 (18)
C2—C3—C4	116.89 (19)	C12—C11—H11	119.7
C2—C3—H3	121.6	C10—C11—H11	119.7
C4—C3—H3	121.6	C11—C12—C13	121.98 (18)
C5—C4—C3	122.5 (2)	C11—C12—H12	119.0
C5—C4—H4	118.7	C13—C12—H12	119.0
C3—C4—H4	118.7	C14—C13—C12	117.42 (18)
C4—C5—C6	118.83 (19)	C14—C13—C16	120.94 (19)
C4—C5—C8	120.96 (17)	C12—C13—C16	121.64 (18)
C6—C5—C8	120.17 (17)	C13—C14—C15	121.17 (18)
C1—C6—C5	117.52 (17)	C13—C14—H14	119.4
C1—C6—H6	121.2	C15—C14—H14	119.4
C5—C6—H6	121.2	C14—C15—C10	121.30 (17)
O1—C7—O2	108.35 (18)	C14—C15—H15	119.4
O1—C7—H7A	110.0	C10—C15—H15	119.4
O2—C7—H7A	110.0	C13—C16—H16A	109.5
O1—C7—H7B	110.0	C13—C16—H16B	109.5
O2—C7—H7B	110.0	H16A—C16—H16B	109.5
H7A—C7—H7B	108.4	C13—C16—H16C	109.5
N1—C8—C5	112.19 (14)	H16A—C16—H16C	109.5
N1—C8—H8A	109.2	H16B—C16—H16C	109.5

C7—O1—C1—C6	172.16 (19)	C9—N1—C8—C5	93.3 (2)
C7—O1—C1—C2	−9.7 (2)	C4—C5—C8—N1	108.75 (19)
C6—C1—C2—C3	1.8 (3)	C6—C5—C8—N1	−68.9 (2)
O1—C1—C2—C3	−176.41 (17)	C8—N1—C9—O3	2.1 (3)
C6—C1—C2—O2	179.79 (16)	C8—N1—C9—C10	−176.54 (15)
O1—C1—C2—O2	1.6 (2)	O3—C9—C10—C15	20.0 (3)
C7—O2—C2—C3	−174.9 (2)	N1—C9—C10—C15	−161.38 (17)
C7—O2—C2—C1	7.3 (2)	O3—C9—C10—C11	−158.13 (18)
C1—C2—C3—C4	−0.9 (3)	N1—C9—C10—C11	20.5 (3)
O2—C2—C3—C4	−178.44 (19)	C15—C10—C11—C12	−0.1 (3)
C2—C3—C4—C5	−0.7 (3)	C9—C10—C11—C12	178.03 (17)
C3—C4—C5—C6	1.5 (3)	C10—C11—C12—C13	0.6 (3)
C3—C4—C5—C8	−176.20 (18)	C11—C12—C13—C14	0.0 (3)
C2—C1—C6—C5	−1.0 (3)	C11—C12—C13—C16	−179.77 (18)
O1—C1—C6—C5	176.87 (17)	C12—C13—C14—C15	−1.1 (3)
C4—C5—C6—C1	−0.6 (3)	C16—C13—C14—C15	178.62 (18)
C8—C5—C6—C1	177.12 (16)	C13—C14—C15—C10	1.7 (3)
C1—O1—C7—O2	14.2 (2)	C11—C10—C15—C14	−1.1 (3)
C2—O2—C7—O1	−13.3 (2)	C9—C10—C15—C14	−179.27 (17)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.91	2.08	2.958 (2)	162
C7—H7A···Cg1	0.97	2.74	3.603 (3)	149
C16—H16C···Cg2	0.96	2.96	3.829 (2)	151

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅NO₃
M_r	269.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	290
a, b, c (Å)	4.9810 (2), 26.652 (1), 10.0545 (3)
β (°)	92.139 (2)
V (Å³)	1333.84 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.33 × 0.24 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Numerical (SADABS; Sheldrick, 1996)
T_min, T_max	0.940, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	4550, 2602, 1698
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 1.03
No. of reflections	2602
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: COLLECT (Nonius, 1999), SCALEPACK (Otwinowski & Minor, 1997), DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012)\bbr00, Marvinsketch (Chemaxon, 2010) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3ⁱ	0.91	2.08	2.958 (2)	162
C7—H7A···Cg1	0.97	2.74	3.603 (3)	149
C16—H16C···Cg2	0.96	2.96	3.829 (2)	151

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

We thank the Brazilian agencies CNPq (140925/2009–0 to SHM), FAPESP and CAPES for financial support. We also thank Professor Carlos A. De Simone for the data collection.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
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